14804-39-8

Basic information

• Product Name: 2,6-DIMETHYL-4-NITROANISOLE
• Synonyms: 2,6-DIMETHYL-4-NITROANISOLE;m-Xylene, 2-methoxy-5-nitro-,;2-Methoxy-1,3-diMethyl-5-nitrobenzene;2,6-dimethyl-4-nitrophenyl methyl ether
• CAS NO: 14804-39-8
• Molecular Formula: C₉H₁₁NO₃
• Molecular Weight: 181.19
• Mol File: 14804-39-8.mol
• Article Data: 15

Chemical Properties

• Melting Point: 85-89°C
• Boiling Point: 299.6°Cat760mmHg
• Flash Point: 138.7°C
• Appearance: /
• Density: 1.148g/cm³
• Vapor Pressure: 0.0021mmHg at 25°C
• Refractive Index: 1.534
• CAS DataBase Reference: 2,6-DIMETHYL-4-NITROANISOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DIMETHYL-4-NITROANISOLE(14804-39-8)
• EPA Substance Registry System: 2,6-DIMETHYL-4-NITROANISOLE(14804-39-8)

Safety Data

• Hazardous Substances Data: 14804-39-8(Hazardous Substances Data)

Usage

General Description

2,6-Dimethyl-4-nitroanisole is a synthetic, aromatic, organic compound with the molecular formula C9H11NO3. This chemical has a variety of applications due to its chemically reactive nature. It contains two methyl groups, an anisole group, and a nitro group, which can exhibit different reactivity depending on the conditions. However, while useful in chemical synthesis, like in dye production, nitroanisoles may also pose certain hazards. Notably, nitroanisoles can be explosive under specific conditions, and potential health risks may also be associated with exposure, depending on specific compound and concentration.

InChI:InChI=1/C9H11NO3/c1-6-4-8(10(11)12)5-7(2)9(6)13-3/h4-5H,1-3H3

Upstream product

• 1004-66-6 2-methoxy-1,3-dimethylbenzene 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 16947-63-0 2,6-dimethyl-4-nitroaniline 
• 77-78-1 dimethyl sulfate 
• 512-56-1 trimethyl phosphite 
• 2423-71-4 2,6-dimethyl-4-nitro phenol 
• 5399-03-1 2-iodo-1-methoxy-4-nitrobenzene 
• 616-38-6 carbonic acid dimethyl ester 
• 39785-37-0 4-amino-2,6-dimethylanisole 
• 92100-74-8 5-(tert-butyl)-2-methoxy-1,3-dimethylbenzene 
• 55215-54-8 5-iodo-2-methoxy-1,3-dimethylbenzene 
• 74-88-4 methyl iodide 
• 14804-38-7 5-bromo-2-methoxy-1,3-dimethylbenzene 

Downstream Products

• 2423-71-4 2,6-dimethyl-4-nitro phenol 
• 39785-37-0 4-amino-2,6-dimethylanisole 
• 23019-47-8 N-acetyl-4-methoxy-3,5-dimethylaniline 
• 854854-83-4 4-methoxy-3,5-dimethyl-2-nitro-aniline 
• 860580-43-4 acetic acid-(4-methoxy-2-nitro-3,5-dimethyl-anilide) 
• 87025-11-4 3,5-dibromo-2,6-dimethylphenol 
• 1170950-10-3 (±)-4-acetamido-3-amino-2,6-dimethyl-5-[3’,4’-dihydroxy-3’-methylbut-1’-yl]anisole 
• 1170950-07-8 (±)-4-acetamido-2,6-dimethyl-5-[3’,4’-dihydroxy-3’-methylbut-1’-yn-1’-yl]-3-nitroanisole 
• 1170949-99-1 4-acetamido-2,6-dimethyl-5-iodo-3-nitroanisole 

Relevant articles and documents

Medium-Sized Cyclophanes. 43. First Evidence for anti-syn-Ring Inversion under the Nitration of 5,13-Di-tert-butyl-8,16-dimethoxy[2.2]metacyclophane

Nitration of 5,13-di-tert-butyl-8,16-dimethoxy[2.2]MCP (metacyclophane = MCP) (1) with various nitrating reagents led to ipso-nitration at the tert-butyl group to give 5-tert-butyl-8,16-dimethoxy-13-nitro[2.2]MCP (2), as well as the corresponding 8,16-epo

A Mild Heteroatom (O -, N -, and S -) Methylation Protocol Using Trimethyl Phosphate (TMP)-Ca(OH) 2Combination

A mild heteroatom methylation protocol using trimethyl phosphate (TMP)-Ca(OH)2combination has been developed, which proceeds in DMF, or water, or under neat conditions, at 80 °C or at room temperature. A series of O-, N-, and S-nucleophiles, including phenols, sulfonamides, N-heterocycles, such as 9H-carbazole, indole derivatives, and 1,8-naphthalimide, and aryl/alkyl thiols, are suitable substrates for this protocol. The high efficiency, operational simplicity, scalability, cost-efficiency, and environmentally friendly nature of this protocol make it an attractive alternative to the conventional base-promoted heteroatom methylation procedures.

Pd-Catalyzed ipso, meta-Dimethylation of ortho-Substituted Iodoarenes via a Base-Controlled C-H Activation Cascade with Dimethyl Carbonate as the Methyl Source

A methyl group can have a profound impact on the pharmacological properties of organic molecules. Hence, developing methylation methods and methylating reagents is essential in medicinal chemistry. We report a palladium-catalyzed dimethylation reaction of ortho-substituted iodoarenes using dimethyl carbonate as a methyl source. In the presence of K2CO3 as a base, iodoarenes are dimethylated at the ipso- and meta-positions of the iodo group, which represents a novel strategy for meta-C-H methylation. With KOAc as the base, subsequent oxidative C(sp3)-H/C(sp3)-H coupling occurs; in this case, the overall transformation achieves triple C-H activation to form three new C-C bonds. These reactions allow expedient access to 2,6-dimethylated phenols, 2,3-dihydrobenzofurans, and indanes, which are ubiquitous structural motifs and essential synthetic intermediates of biologically and pharmacologically active compounds.

Palladium-Catalyzed 4-Fold Domino Reaction for the Synthesis of a Polymeric Double Switch

A palladium-catalyzed 4-fold domino reaction consisting of two carbopalladation reactions and two C-H activation reactions, followed by the introduction of an acrylate moiety, led to the tetra-substituted helical alkene A2, using the dialkyne A3 as a subs